50 | The Courage to Pivot: Discernment in Entrepreneurship and Leadership with Jill Simons

Have you ever built something successful… only to realize it may not be the thing you’re meant to keep building? Do you ever feel the tension between what’s working externally and what feels truly aligned internally? For many leaders and entrepreneurs, there comes a moment when growth requires something deeper than strategy—it requires discernment, courage, and the willingness to let go of what no longer fits.  If you’ve ever faced a leadership pivot, questioned your direction, or wondered how to build a team where everyone’s gifts can truly flourish, this conversation will resonate deeply. In this episode, Anna interviews Jill Simons, founder and executive director of Many Parts Ministries, to explore the real, human side of leadership transitions - those pivotal moments when entrepreneurs and leaders sense it’s time to let go, pivot, or begin again.  Together, they discuss discernment, charisms, team culture, and how leaders can build organizations that truly honor the gifts of the people within them.    This conversation offers a refreshing vision of leadership that is deeply human, deeply Catholic, and rooted in the belief that every person has meaningful gifts to contribute to the mission.  If your business or organization is at a pivotal growth point—and you’re craving strategic clarity, structure, or leadership support to scale your mission sustainably— 👉 Learn about Strategic Mapping™Not sure what you need, but want to connect and begin the conversation? Let's explore what your needs are, and how we can help!  👉 Book a discovery call with Anna